Food Chemistry 211 (2016) 124–129

Contents lists available at ScienceDirect

Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Mechanism of formation of 3-chloropropan-1,2-diol (3-MCPD) esters

under conditions of the vegetable oil refining
Jan Šmidrkal ⇑, Markéta Tesařová, Iveta Hrádková, Markéta Berčíková, Aneta Adamčíková, Vladimír Filip
Department of Dairy, Fat and Cosmetics, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague, Czech Republic

a r t i c l e i n f o a b s t r a c t

Article history: 3-MCPD esters are contaminants that can form during refining of vegetable oils in the deodorization step.
Received 10 June 2015 It was experimentally shown that their content in the vegetable oil depends on the acid value of the veg-
Received in revised form 18 April 2016 etable oil and the chloride content. 3-MCPD esters form approximately 2–5 times faster from diacylglyc-
Accepted 3 May 2016
erols than from monoacylglycerols. It has been proved that the higher fatty acids content in the oil caused
Available online 6 May 2016
higher 3-MCPD esters content in the deodorization step. Neutralization of free fatty acids in the vegetable
oil before the deodorization step by alkaline carbonates or hydrogen carbonates can completely suppress
Keywords:
the formation of 3-MCPD esters. Potassium salts are more effective than sodium salts.
3-Chloropropane-1
2-Dipalmitate
Ó 2016 Elsevier Ltd. All rights reserved.
3-Chloropropane-1
2-Diol
3-MCPD esters
3-CPD esters
Deodorization
Refining
Palm oil

1. Introduction
Esters of higher fatty acids and 3-chloropropan-1,2-diol (3-
MCPD) are contaminants, which form during refining of vegetable
oil in the deodorization step (Franke, Strijowski, Fleck, & Pudel,
2009; Matthaus, Pudel, Fehling, Vosmann, & Freudenstein, 2011)
and/or physical refining. Deodorization is water steam distillation
of volatile substances, during which the superheated water steam
at temperature 180–260 °C is introduced under lowered pressure
(3–20 mbar) into vegetable oil at temperature 180–260 °C.
The International Agency for Research on Cancer (IARC)
characterizes 3-MCPD as possibly carcinogenic to humans, based
on cancer incidents caused by 3-MCPD in laboratory animals (renal
tubular tumors, Leyding cell adenomas). 3-MCPD́s metabolite,
glycidol, is also characterized by IARC as possibly carcinogenic to
humans (IARC Monographs, 2012). Research on 3-MCPD has been
Abbreviations: DAG, diacylglycerol; DPG, 1,3-dipalmitoylglycerol,1,3-dipalmi
tin; HOSO, high oleic sunflower oil; HPC, (totally) hydrogenated palmstearin; MAG,
monoacylglycerol; MPG, 1-palmitoylglycerol, 1-monopalmitin; MESO, sunflower oil
methyl esters; TAG, triacylglycerol; TBAC, tetrabutylammonium chloride; TPG,
tripalmitoylglycerol, tripalmitin; 3-MCPD, 3-chloro-1,2-propandiol; 2-MCPD, 2-
chloro-1,3-propandiol.
⇑ Corresponding author.
E-mail address: jan.smidrkal@vscht.cz (J. Šmidrkal).
intensive in the past 10 years, and many countries already have
regulations on the levels of 3-MCPD allowed in food, yet foods with
a high concentration of 3-MCPD are still widely available to con-
sumers. Removal methods must be introduced to ensure that the
concentration of 3-MCPD in foods are within the required levels
(Lee & Khor, 2015).
Vegetable oil contains before deodorization triacylglycerols
(TAG), diacylglycerols (DAG). monoacylglycerols (MAG), (free)
fatty acids and chloride compounds (chlorides, hydrogen chloride),
alternatively organic chloride compounds. Chlorides come from
parts of plants (pulp in cases of palm and olive) from which the
oil was pressed and extracted; the free hydrogen chloride come
from bleaching earth, by which the oil was bleached (Collison,
2010).
The concentration of 3-MCPD esters in vegetable oil after
deodorization depends on the composition of the vegetable oil. In
rapeseed oil, which contains only 2% of diacylglycerols and 0.1% of
(free) fatty acids, the content of 3-MCPD esters as free 3-MCPD
increases from 0.4 to 1.0 ppm. On the contrary, in palm oil, which
consists of 5% of diacylglycerols and 0.24% of (free) fatty acids, the
content of 3-MCPD increases from 1.0–4.4 ppm (Franke et al.,
2009).
Literature indicates that 3-MCPD esters form from DAG and
TAG (Rahn & Yaylayan, 2013), from MAG and DAG (Freudenstein,

http://dx.doi.org/10.1016/j.foodchem.2016.05.039
0308-8146/Ó 2016 Elsevier Ltd. All rights reserved.
 J. Šmidrkal et al. / Food Chemistry 211 (2016) 124–129 125

Weking, & Matthaus, 2013; Hamlet et al., 2011; Matthaus et al.
2011; Shimizu, Vosmann, & Matthaus, 2012; Shimizu, Weitkamp,
Vosmann, & Matthaus, 2013; Smidrkal et al., 2011) or from TAG
(Destaillats, Craft, Sandoz, & Nagy, 2012). There is a disagreement
on whether free fatty acids are (Smidrkal et al., 2011) or are not
(Freudenstein et al., 2013) the direct precursors of 3-MCPD esters
formation.
To find out from which acylglycerol type the 3-MCPD esters
form and if fatty acids influence their formation, experiments in
inert conditions were carried out. The mixture of sunflower oil
methyl esters with high content of oil acid (MESO) was chosen as
the inert medium. The sunflower oil methyl esters were prepared
by transesterification of the sunflower oil. The tetrabutylammo-
nium chloride (TBAC) was the source of the chlorine; palmitic
acid was used as the fatty acid of choice. The following
reference acylglycerols (1-monopalmitoylglycerol (MPG), 1,3-
dipalmitoylglycerol (DPG) and 1,2,3-tripalmitoylglycerol) were
synthetized as pure substances. The above mentioned compounds
were subsequently heated (240 °C) in various combinations in a
reactor. Samples were taken in regular time intervals. The content
of free 3-MCPD formed during 3-MCPD ester hydrolysis was deter-
mined in the samples.
Fatty acids split off a proton more easily at higher temperatures
(>150 °C) and their acidity increases to the level of strong acids; as
a result, they are able to catalyze esterification (De, Bhattacharyya,
& Bandyopadhyay, 2002; Thomas & Sudborough, 1912).
This paper attempts to explain the origin of hydrogen chloride.
We hypothesize that during the deodorization the equilibrium
between a fatty acid and sodium chloride is established and fatty
acid salt with hydrogen chloride is formed. The hydrogen chloride
subsequently reacts with acylglycerol (the fastest reaction is with
diacylglycerol). The necessary prerequisite of the reaction is the
presence of fatty acid (RCOOH) and ionic bound chlorine (e.g. NaCl,
KCl, TBAC), or maybe the presence of free hydrogen chloride.
2. Materials and methods
2.1. Chemicals
refractometrically. The refractive index readings stabilized after
1 h. Hydrogenation continued for an additional 1 h; then the reac-
tion mixture was cooled down to 70 °C and the catalyst was fil-
tered off. The analytical parameters of HPS are listed in the
Tables S1 and S2.
2.2. Model deodorization
2.2.1. Model reactor
The model reactor was a vertical glass tube (length: 220 mm,
inner diameter: 20 mm) fitted at the bottom with an argon feeding
tube and sintered glass, and at the top with a tapered ground joint
and an outlet tube (see Supplementary material Fig. S1) placed in
an air bath adapted from an old GLC.
Small amounts of reactants (<300 mg) were added together
using a small weighing dish, as such small amounts could not be
accurately weighed separately.
2.2.2. Model deodorization ((MESO + MAG + 0.1% TBAC – acid value
1.0 mg KOH
g 1)
The MESO (14.5 g) was introduced into the reactor heated to
140 °C with argon inlet, then MPG (0.46 g, 1.4 mmol) was added
and the temperature was increased to 240 °C within 15 min. Sub-
sequently, first TBAC (15 mg, 0.054 mmol) and – after 30 s – palmi-
tic acid (48 mg, 0.19 mmol) were added. After 1 min the first
sample (time 0) was taken and immediately cooled down to a
room temperature. Subsequent samples were taken in given time
intervals.
The amount of palmitic acid required to obtain acid values 0.3;
1.0; 2.0 and 4.0 mg KOH g 1 was 0, 48, 117 and 254 mg,
respectively.
For additional experiments, the amount of MESO and DPG was
14.2 and 0.80 g (1.4 mmol), in the case of MESO and HPS the
amount was 13.8 and 1.18 g (0.14 mol).
The testing of acylglycerol suitability was performed under the
same conditions (see Fig. 1).

The following chemicals used were all products of Sigma-

2.2.3. Model deodorization (HOSO + 0.1%TBAC + KHCO3)
Aldrich Co (Steinhemi, Germany): palmitic acid (>99%), tetrabuty-
The HOSO (15 g) was introduced into the reactor at room tem-
lammonium chloride (P97%), Na2CO3 (>99.5%), NaHCO3 (>99.5%),
perature and with an argon inlet and the temperature was
KHCO3 (>99.5%), K2CO3 (>99%). Palmstearin used was the product
increased to 240 °C. TBAC (15 mg, 0.054 mmol) and – after 30 s –
of AarhusKarlshamm (Czech Republic). Sunflower oil with high
KHCO3 (3.8 mg, 0.038 mmol) were added. Sampling protocol was
content of oleic acid was the product of Palma Group (Bratislava,
as described above.
Slovakia).

2.1.1. Sunflower oil methyl esters with high content of oleic acid
(MESO)
The mixture of sunflower oil (acid value 0.2 mg KOH g 1, 0,05%
H2O, 1000 g, 1.2 mol), methanol (0.05% H2O, 292 ml, 7.2 mol) and
potassium hydroxide (12.2 g, 0.22 mol) was stirred for 2 h in nitro-
gen atmosphere. After separation of the bottom glycerol phase, the
upper ester phase was washed with distilled water (5  200 ml) to
neutral reaction. After drying with sodium sulphate, the product
was distilled in vacuum and the fraction was collected at 166–
170 °C/100 Pa (880 g). The analytical parameters of MESO are
listed in the Tables S1 and S2.

2.1.2. Hydrogenated palmstearin (HPS)

Nickel catalyst (4 g) was added at the temperature of 150 °C to
the molten palmstearin (acid value 0.6 mg KOH g 1, 200 g) and
bubbled through by hydrogen (20 L
h 1). Subsequently, the tem-
perature was increased to 180 °C and the flow of hydrogen was
increased to 80 L
h 1. The hydrogenation process was monitored Fig. 1. Testing of used MESO and acylglycerols (blank experiment).
126 J. Šmidrkal et al. / Food Chemistry 211 (2016) 124–129

In subsequent experiments 3.2 mg (0.037 mmol) of NaHCO3,
2.0 mg (0.037 mmol) of Na2CO3 and 2.6 mg (0.037 mmol) of
K2CO3 were used.
2.3. Preparation of tested compounds
Sunflower oil methyl esters were prepared using oil transester-
ification by methanol with potassium hydroxide as a catalyst.
1-Monopalmitin (MPG) was prepared using a two-step synthe-
sis described by Mori (2012). 2,2-Dimethyl-1,3-dioxolan-4-methy
l-hexadecanoate was prepared using acylation of 2,2-dimethyl-1,
3-dioxolan-4-methanol by palmitoyl chloride. In the subsequent
step the protecting acetonide group was removed by hydrolysis
of 80% citric acid.
1,3-Dipalmitin (DPG) was also prepared using the 2-step syn-
thesis (Mank, Ward, & Van Dorp, 1976). Glycidyl palmitate was
prepared by acylation of freshly distilled glycidol by palmitoyl
chloride. 1,3-Dipalmitin forms by reaction of glycidyl palmitate
with palmitic acid.
Tripalmitin (TPG) was prepared by using the above described
acylation (Mank et al., 1976) of 1,3-dipalmitin by palmitoyl
chloride.
Hydrogenated palmstearin was prepared (HPS) by palmstearin
hydrogenation.
2.4. Analytical procedures
The composition of the acylglycerols used was determined
using the TLC-FID method on the Iatroscan apparatus (Iatron Lab-
oratories, Inc., Tokyo, Japan) with the S II sticks and the mobile
phase consisting of hexane/diethylether/formic acid in the ratio
of 92:8:1 (v/v/v).
The amount of 3-MCPD was determined using the method
described in Smidrkal et al., 2011. Each experiment was repeated
3 times and relative error was ±5%.
Fig. 2, prove that 3-MCPD esters were not formed from MESO
(see MESO and MESO + 0.1% TBAC, Fig. 1).
While testing acylglycerols in MESO with TBAC present
(Fig. 2a–c) it was shown that 3-MCPD esters do not form from
either MPG or DPG, however, higher amount of 3-MCPD esters
formed from TPG. This was probably due to the fact that TPG
was prepared in reaction of 1,3-dipalmitin and palmitoyl chloride
with pyridine present. The traces of chlorine compounds (incl. 3-
MCPD esters) probably remained in TPG, from which subsequently
higher amount of 3-MCPD esters formed during the model deodor-
ization. This is why triacylglycerol (HPS) prepared by total hydro-
genation of palmstearin was used, as during this process 3-MCPD
esters do not form in higher amounts (Fig. 2a–c).
Under conditions of model deodorization (240 °C), individual
acylglycerols were tested with different content of free fatty acids
(acid value 0.3–4.0 mg KOH
g 1; acid value increased when palmi-
tic acid was added). This clearly proves that as the acid value
increased (with higher content of free fatty acids), the content of
3-MCPD esters also increased (Fig. 2a–c).
The results (Fig. 2a–c) also indicate that 3-MCPD esters form
approximately 2–5 times faster from DPG than from MPG depend-
ing on the acid value. For similar results see Freudenstein et al.,
2013. For comparison, dependence of maximum 3-MCPD amount
on acid number of reactive mixture in time 0.5 h is shown (Fig 3).
So far it is not clear, whether 3-MCPD esters (in the case of HPS)
form from major amount of TAG or minor amount of DAG. In the
case of MPG, which does not contain detectable traces of DPG or

3. Results

3.1. Model deodorization of acylglycerols

The tested mixtures of MESO and acylglycerols (Fig. 2a–c) con-

tained the same amount of acylglycerols (1.4 mmol of acylglycerol
per 15 g of reaction mixture).
It was demonstrated that under conditions of model deodoriza-
tion methyl esters (MESO) do not contain traces of MAG, DAG or
TAG, from which 3-MCPD esters can be formed by reaction with
tetrabutylammonium chloride (TBAC). The results, shown in the Fig. 3. Content of 3-MCPD at 0.5 h depending of acid value.

Fig. 2. Model deodorization of MPG (a), DPG (b) and HPS (c) based on different acid values.
 J. Šmidrkal et al. / Food Chemistry 211 (2016) 124–129 127

TPG, it is evident that 3-MCPD esters (monoesters) form from MPG. detectable amount of monoacylglycerols. In this case 3-MCPD
In the case of triacylglycerol (HPS), the situation is more compli- esters can form either from minor amount of diacylglycerols or
cated. HPS contains 1.1% of diacylglycerols and does not contain from major amount of triacylglycerols.

Fig. 4. Model deodorization of HOSO at different content of TBAC (a) and neutralized by alkali carbonates and hydrogencarbonates (b).

The presumed way of origin hydrogen chloride

O O
- +
R O H R OH Dissociation of fatty acid

O O
- + + - - +
R OH + Na Cl R O Na + H Cl Origin of hydrogen chloride

monoacylglycerol O diacylglycerol O triacylglycerol

HO O R O O R O O
O H O H O O H
H R O Cl H R O Cl R O Cl
R
O O
- -
Cl-
HO O Cl R O O Cl R O O
O + O + O O +
H R O H H R O H R O H
R impropable
O O

HO R O R O Cl-
O O O
+ H + H + H
Cl- O O Cl- O O O O O
H H R R
R
R impropable
O O
- -
Cl Cl Cl-
HO O R O O R O O
+ H O + H + H
less O O more O O O
probable probable R 2
R H attack,
H R R
attack,
more less O
sterically sterically Cl- Cl-
hiderd Cl- hindered O Cl- O
atom atom
+ +
HO O HO O R O O R O O
+ +
O O O O
R R R R
O O

HO O HO Cl R O O R O Cl
Cl O O Cl O O
R O R O
R R
2-MCPD monoester 3-MCPD monoester 2-MCPD diester 3-MCPD diester

Fig. 5. Expected mechanism of MCPD esters formation.

128 J. Šmidrkal et al. / Food Chemistry 211 (2016) 124–129
O O
R H
H O R O
O O
H O
O
1-monoacylglycerol 1-monoacyglycerol
Fig. 6. Formation of hydrogen bonds in monoacylglycerol and diacylglycerol molecules.
3.2. Model deodorization of high oleic acid sunflower oil
Formation of 3-MCPD esters from refined sunflower oil with
high content of oleic acid (HOSO - acid value 0.14 mg KOH g 1,
0.3% DAG and 0.28 mg 3-MCPD kg 1) was tested under the same
conditions. The content of 3-MCPD during a blank experiment
was at the same level (see Franke et al., 2009) (Fig. 4a, 0.000%
TBAC). Depending on the increasing amount of TBAC, the content
of 3-MCPD esters increased.
In another experiment, free fatty acids in HOSO were neutral-
ized by alkaline carbonates (in equimolar content according to
the acid value). We conclude (Fig. 4b) that NaHCO3 is only slightly
more efficient than Na2CO3, while potassium salts KHCO3 and
K2CO3 are much more efficient than sodium analogues. The higher
efficiency of potassium salts is probably caused by their faster dis-
solution in the reactive mixture and higher alkalinity.
Both potassium salts (KHCO3 and K2CO3) can be used to sup-
press and eliminate the 3-MCPD formation as described in
Smidrkal et al. (2011); and Smidrkal et al. (2012).
4. Discussion
The above results support the possible existence of the follow-
ing mechanism of 3-MCPD esters formation (Fig. 5). First, the equi-
librium between a fatty acid and sodium chloride is established
and hydrogen chloride is formed. Subsequently, the oxygen atom
of glycerol oxo group is protonated. Then a 1,3-dioxolan cycle is
created with a participation of the hydroxyl group.
After water is split off (in the case of monoacylglycerol and dia-
cylglycerol), a cyclic oxonium ion forms. After the nucleophilic
substitution by the chloride anion the cycle oxonium (less steri-
cally hindered carbon atom with the ring open) yields either
monoester or a 3-MCPD diester. In the same manner, though to a
lesser extent, the nucleophilic substitution at the more sterically
hindered carbon atom yields monoester or a 2-MCPD diester
(Fig. 5).
Theoretically, 1,3-dioxolane may be also formed from triacyl-
glycerols. However, nucleophilic attack of an oxygen atom ester
group, which has a decreased electron density due to the oxo
group, is unlikely. Carboxylic acid would have to split off from
the formed 1,3-dioxolane group, for the oxygen atom of the oxo
group to be able to attack nucleophilically the oxygen atom of
the ester oxo group. Although the electron density of the carbon
atom is decreased by the positively charged neighbouring oxygen
atom, simultaneously the electron density is increased by the
neighboring alkyl group. Thus, such attack being unlikely, the for-
mation of 3-MCPD esters from TAG is unlikely, however, this the-
ory needs to be verified experimentally yet.
Lower rate of 3-MCPD ester formation from monoacylglycerols
than from diacylglycerols can be explained by the lower electron
density on the oxygen atom of the monoacylglycerol oxo group
(Fig. 6). Electron density of the oxygen atom of the monoacyglyc-
erol oxo group is decreased by the hydrogen bridges, which can
be formed by the oxygen atom of the oxo group reacting with
the hydrogen atoms of primary and secondary monoacylglycerol
hydroxyl group. In diacyglycerols the hydrogen atom of the hydro-
xyl group can form a hydrogen bridge only with an oxygen atom of
O O R
R
H O
H O
O
1,3-diacylglycerol
one group of oxo group, an oxygen atom of the other oxo group is
free and does not decrease electron density. Thus the oxygen atom
protonates more easily.
5. Conclusions
Presence of fatty acids (or possibly free hydrogen chloride) is
necessary for formation of 3-MCPD ester. As the amount of free
fatty acids increases, the amount of 3-MCPD esters also increases.
3-MCPD amount increases (when the amount of free fatty acids is
constant) with increasing amount of chlorides. 3-MCPD esters are
formed 2–5 times faster from diacylglycerols than from monoacyl-
glycerols (or possibly from triacylglycerols). Whether 3-MCPD
esters are formed from the major triacylglycerol or the minor dia-
cylglycerol present in the major triacyglycerol needs to be exam-
ined yet. 3-MCPD esters decomposed during reaction time; the
rate of decomposition process increased with the rising amount
of free fatty acids. It has been proved that the higher fatty acids
content in the oil caused higher 3-MCPD esters content in the
deodorization step. Sodium hydrogen carbonate and sodium car-
bonate (the amount needed to neutralize fatty acids and possibly
the hydrogen chloride present) decrease the velocity of 3-MCPD
ester formation and slowly leads to decomposition of the formed
3-MCPD esters. Potassium hydrogen carbonate and potassium car-
bonate (in the amounts needed to neutralize the present acids)
prevent completely the 3-MCPD ester formation.
Conflict of interest
The authors have declared no conflict of interest.
Appendix A. Supplementary data
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.foodchem.2016.
05.039.
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